One of the most common questions that people ask after they decide to deploy SharePoint is “Can I upload my existing documents to SharePoint”. The answer is “Yes”. The very next question is “Do I have to do them one at a time?”. The answer is “No, provided you have Office software installed on the machine you plan to use to upload”.
If you access a SharePoint document library from a machine without Office installed and select Upload from the menu you will only see one option like so:
However, if you repeat the process using a machine that has Office installed you will see two menu options like so:
Typically, you’ll get the first option when you access SharePoint from a server machine, thinking you can do the uploads from there. Better option is to go to a workstation and use the Upload Multiple Documents so you can transfer your documents up to SharePoint in one hit.